John Oliver Is Finally Ready to Take on Donald Trump

In June 2015, Donald Trump announced his presidential bid to the immense amusement of the national media, which promptly launched into weeks of talking-head debates on 24-hour news networks. Over the next seven months, Jeb (!) Bush became the frontrunner, then the loser; Ben Carson bumbled his way up to serious-candidate status; Trump became the joke, then the frontrunner; Cruz rose from the muck to win Iowa; and thirteen other Republican candidates jockeyed below them in the polls. Meanwhile, John Oliver ignored this enormous wealth of comedic gold, instead focusing on subjects like transgender rights, mental health, refugees, and the dark world of Internet bullying. He never touched the presidential election on his Sunday night HBO show Last Week Tonight. He made a point not to.

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"No part of me thought it would be great to cover this massively overblown occasion," Oliver said at a media breakfast at the HBO offices in New York on Wednesday. "There are all the ways to get lost in the general campaign ephemera where nothing is happening of significant consequence. We were much happier concentrating on other things that seemed a bit more relevant last year."

Things like interviewing Edward Snowden, government surveillance, televangelists, and the uselessness of pennies. Throughout the season Oliver—who, like his mentors Jon Stewart and Stephen Colbert, does not identify himself as a journalist—brought attention to key stories that the public and the media were all but ignoring. But now, as the show kicks off its third season on February 14, Oliver won't ignore the election any longer.

"It's finally appropriate," he says, "But I think we'll do more stuff that has to do with the process and the personalities. I don't think we'll do too much on the daily dramas of the campaign."

Such pointed skewering is needed now more than ever. Trevor Noah's The Daily Show is following in Stewart's giant steps and is still finding its footing, to mixed results. "Jon Stewart: That is a massive, massive figurehead leaving. The show is in a rebuilding mode," said Oliver, who admits that he doesn't watch Noah's iteration. That leaves viewers hungry for the withering political satire they once relied on Stewart to deliver.

And Oliver might just be our man. As it's always done, Last Week Tonight will look for underreported trends. The extended segments for which it's known don't cover the viral stories, they become the viral stories (though Oliver mentioned his disdain for the "Oliver Eviscerates," or "Oliver Dismantles" headlines that inevitably pop up each Monday morning). But that also means that Oliver will have to take on Trump—who's called the show "very boring," a quote which they've placed on their posters.

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"I don't think that you can claim that he doesn't exist, no matter how hard your mind tries," Oliver said. But is he worried that Trump might be our next president? "I don't think that's going to be a problem that we're going to have to deal with...I'm less interested with what he is saying than what is happening underneath."

Oliver said he's landed at the perfect place to do this, because HBO doesn't care about what he does so long as it's smart and insightful. "'You can do whatever you'd like.' You get told that a lot. And you presume HBO is lying, and then it just happens where they don't say anything and they let us do everything."

For example, Oliver's now-famous interview with Edward Snowden, which came as a surprise not just to viewers but to HBO executives as well. Without telling anyone but a few close associates, Oliver planned a meeting with the government whistleblower—and international fugitive—with a small crew in Russia. "From a U.S. perspective, you're not really supposed to do it. It's like basic level parenting. Don't stare directly at the sun and don't meet fugitives," Oliver said. "It was a panicky 36 hours there, so we split the tapes between us in case any of us got stopped."

Oliver and his staff—some of which come from New York Times Magazine, ProPublica, CNN and MSNBC—have been hard at work on the new season, researching, reporting, and fact checking stories. "It doesn't sound funny, that's for sure. The funny comes later," Oliver said. "You have to make sure you're structurally sound first. You can write jokes late. That's my only job. Structuring a story is different. If the elements of a story collapse it takes all the jokes down with it."

Though it sounds like an investigative unit, Oliver will be the first to assure you that it's not. This is comedy.

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